Pentomone

In this article we are going to delve into the topic of Pentomone and explore its many facets. Pentomone is a topic that has aroused great interest in various areas, from science to popular culture. Throughout history, Pentomone has been the subject of debate, research and reflection, and remains relevant today. We will delve into the different perspectives that exist on Pentomone, addressing its importance, its implications and its impact on society. Through this article, we aim to offer a comprehensive and updated vision of Pentomone, with the aim of enriching knowledge and promoting reflection on this fascinating topic.

Pentomone
Clinical data
Other namesLilly 113935; LY-113935
Drug classNonsteroidal antiandrogen
ATC code
  • None
Identifiers
  • (5aS,6aR,12aS,13aR)-4,8-dimethoxy-6,6-dimethyl-5a,6a,12,12a,13a,14-hexahydrochromenoxanthen-13-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC24H26O5
Molar mass394.467 g·mol−1
3D model (JSmol)
  • CC1(C2C(CC3=C(O2)C(=CC=C3)OC)C(=O)C4C1OC5=C(C4)C=CC=C5OC)C
  • InChI=InChI=1S/C24H26O5/c1-24(2)22-15(11-13-7-5-9-17(26-3)20(13)28-22)19(25)16-12-14-8-6-10-18(27-4)21(14)29-23(16)24/h5-10,15-16,22-23H,11-12H2,1-4H3/t15-,16+,22-,23+
  • Key:MTJTVTZUEKVNTG-YJEDKTMASA-N

Pentomone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (developmental code name Lilly 113935 or LY-113935) is a nonsteroidal antiandrogen (NSAA) described as a "prostate growth inhibitor" which was never marketed. It was synthesized and assayed in 1978.

Synthesis

Condensation of two equivalents of o-vanillin with 4,4-dimethylcyclohexadienone (2) gives the five-ring ketone derivative (3). The reaction may be visualized as initial conjugate addition of phenoxide to the enone followed by interception of the resulting anion by the aldehyde carbonyl group. Catalytic hydrogenation then reduces both olefin pi-bonds as well as the ketone, to give (4). Re-oxidation of the alcohol thus formed with pyridinium chlorochromate affords pentomone.

References

  1. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 949–. ISBN 978-1-4757-2085-3.
  2. ^ Michael E. Flaugh, U.S. patent 4,081,458 (1978 to Eli Lilly And Company).
  3. ^ David A Hall, Richard E Heiney, & Michael E Flaugh, GB1593643 (1981 to Eli Lilly and Co).



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